1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-Chloro-phenyl)-3-methoxy-N-[2-oxo-2-(2-phenyl-pyrrolidin-1-yl)-ethyl]-benzene sulfonamide

HRID 2079606ノート

反応式

HRID 2079606 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:20][C:21](O)=[O:22])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:54]1([CH:60]2[CH2:64][CH2:63][CH2:62][NH:61]2)[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:20][C:21](=[O:22])[N:61]2[CH2:62][CH2:63][CH2:64][CH:60]2[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(=[O:10])=[O:11])=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2618922-PhenylpyrrolidineHCID 57788180[(4-Chlorophenyl)-(3-methoxy-benzenesulfonyl)-amino]-acetic acid

生成物 1

HCID 44197669N-(4-Chloro-phenyl)-3-methoxy-N-[2-oxo-2-(2-phenyl-pyrrolidin-1-yl)-ethyl]-benzene sulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

To a solution of [(4-chlorophenyl)-(3-methoxy-benzenesulfonyl)-amino]-acetic acid (250 mg, 0.7 mmol) in dry dichloromethane (20 mL) were sequentially added EDCI (202 mg, 1.05 mmol), HOBT (142.4 mg, 1.05 mmol), and DIPEA (0.23 mL, 1.40 mmol). The reaction mixture was allowed to stir for 30 minutes under nitrogen at 25° C. 2-Phenyl-pyrrolidine (104 mg, 0.7 mmol) was added and the mixture was stirred at 25° C. for 12 h. The reaction mixture was diluted with dichloromethane (20 mL), washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and water. The organic layer was dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography over silica gel (30-40% ethyl acetate/hexane) to yield the title compound.

後処理

  1. stirringthe mixture was stirred at 25° C. for 12 h
  2. washwashed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel (30-40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-45eec1ad653542c1b3d0b342572f17f0
出典データセット
uspto-grants-2011_04
特許番号
US07932269B2

反応ノート

読み込み中…